US4391809A - Methods for treating psoriasis - Google Patents
Methods for treating psoriasis Download PDFInfo
- Publication number
- US4391809A US4391809A US06/206,596 US20659680A US4391809A US 4391809 A US4391809 A US 4391809A US 20659680 A US20659680 A US 20659680A US 4391809 A US4391809 A US 4391809A
- Authority
- US
- United States
- Prior art keywords
- methyl
- quinazoline
- diamino
- treating psoriasis
- methods
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 8
- 201000004681 Psoriasis Diseases 0.000 title claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- KBKJXVMKCWBZLB-UHFFFAOYSA-N 5-chloro-6-[(3,4-dichloroanilino)methyl]quinazoline-2,4-diamine Chemical compound C1=CC2=NC(N)=NC(N)=C2C(Cl)=C1CNC1=CC=C(Cl)C(Cl)=C1 KBKJXVMKCWBZLB-UHFFFAOYSA-N 0.000 claims abstract description 5
- NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 241000124008 Mammalia Species 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- FXVNLDJOPDKQHF-UHFFFAOYSA-N acetic acid;5-chloro-6-[(3,4-dichloroanilino)methyl]quinazoline-2,4-diamine Chemical compound CC(O)=O.C1=CC2=NC(N)=NC(N)=C2C(Cl)=C1CNC1=CC=C(Cl)C(Cl)=C1 FXVNLDJOPDKQHF-UHFFFAOYSA-N 0.000 claims 1
- LZAHAWHPLGBAQD-UHFFFAOYSA-N acetic acid;5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline-2,4-diamine Chemical compound CC(O)=O.COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 LZAHAWHPLGBAQD-UHFFFAOYSA-N 0.000 claims 1
- 230000002682 anti-psoriatic effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 240000006474 Theobroma bicolor Species 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 239000001761 ethyl methyl cellulose Substances 0.000 description 1
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
Definitions
- the present invention relates to methods for treating psoriasis in mammals, such as dogs, horses, sheep, etc., by administering 2,4-diamino-5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline, 2,4-diamino-5-chloro-6-[(3,4-dichloroanilino)methyl]quinazoline or a pharmaceutically acceptable acid-addition salt thereof.
- pharmaceutically acceptable acid-addition salt is intended to mean any salt form that is prepared from a relatively non-toxic acid, such as the hydrochloride, sulfate, phosphate, benzoate, acetate, citrate, tartrate, etc.
- 2,4-diamino-5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline, 2,4-diamino-5-chloro-6-[(3,4-dichloroanilino)methyl]quinazoline and their pharmaceutically acceptable acid-addition salts can exist in anhydrous forms as well as in solvated (such as an acetate, hydrates, etc.) forms.
- solvated such as an acetate, hydrates, etc.
- the hydrated forms and the solvated forms with pharmaceutically acceptable solvents are equivalent to the anhydrous or unsolvated form for the purposes of the invention and are intended to be within the scope of this invention.
- 2,4-diamino-5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline 2,4-diamino-5-chloro-6-[(3,4-dichloroanilino)methyl]quinazoline or their acid-addition salts may be administered orally with the dosage adjusted for the type of psoriasis and tolerances of the individual patient; the parenteral routes, especially the intravenous route, are most preferred.
- the usual mammalian dosage range for a 70 kg human subject is from 5 to 500 mg per day (0.07 mg to 7.1 mg per kg of weight per day), preferably 15 to 120 mg per day (0.2 mg to 1.7 mg per kg of weight per day), optionally in divided portions.
- Therapeutic agents of this type are generally prescribed for a specific time span, such as for a five day period depending upon the disease state being treated.
- compositions are produced by formulating the active compound in dosage unit form with a pharmaceutical carrier.
- dosage unit forms are tablets, capsules, pills, powders, aqueous and non-aqueous oral solutions and suspensions, and parenteral solutions packaged in containers containing either one or some larger number of dosage units and capable of being subdivided into individual doses.
- suitable pharmaceutical carriers are gelatin capsules; sugars such as lactose and sucrose; starches such as corn starch and potato starch; cellulose derivatives such as sodium carboxymethyl cellulose, ethyl cellulose, methyl cellulose, and cellulose acetate phthalate; gelatin; talc; stearic acid; magnesium stearate; vegetable oils such as peanut oil, cottonseed oil, sesame oil, olive oil, corn oil, and oil of theobroma; propylene glycol; glycerine; sorbitol; polyethylene glycol; water; agar; alginic acid; isotonic saline, and phosphate buffer solutions; as well as other compatible substances normally used in pharmaceutical formulations.
- the compositions of the invention can also contain other components such as coloring agents, flavoring agents, and/or preservatives. These materials, if present, are usually used in relatively small amounts.
- the compositions can, if desired, also contain other therapeutic agents.
- the percentage of the active ingredient in the foregoing compositions can be varied within wide limits but for practical purposes it is preferably present in a concentration of at least 10% in a solid composition and at least 2% in a primarily liquid composition.
- the most satisfactory compositions are those in which a much higher proportion of the active ingredient is present.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Methods for treating psoriasis by administering 2,4-diamino-5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]-quinazoline, 2,4-diamino-5-chloro-6-[(3,4-dichloroanilino)methyl]-quinazoline or a pharmaceutically acceptable acid-addition salt thereof.
Description
This is a continuation of application Ser. No. 84,944 filed Oct. 15, 1979, now abandoned.
The present invention relates to methods for treating psoriasis in mammals, such as dogs, horses, sheep, etc., by administering 2,4-diamino-5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline, 2,4-diamino-5-chloro-6-[(3,4-dichloroanilino)methyl]quinazoline or a pharmaceutically acceptable acid-addition salt thereof.
The term "pharmaceutically acceptable acid-addition salt" is intended to mean any salt form that is prepared from a relatively non-toxic acid, such as the hydrochloride, sulfate, phosphate, benzoate, acetate, citrate, tartrate, etc.
In addition, 2,4-diamino-5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline, 2,4-diamino-5-chloro-6-[(3,4-dichloroanilino)methyl]quinazoline and their pharmaceutically acceptable acid-addition salts can exist in anhydrous forms as well as in solvated (such as an acetate, hydrates, etc.) forms. In general, the hydrated forms and the solvated forms with pharmaceutically acceptable solvents are equivalent to the anhydrous or unsolvated form for the purposes of the invention and are intended to be within the scope of this invention.
While 2,4-diamino-5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline, 2,4-diamino-5-chloro-6-[(3,4-dichloroanilino)methyl]quinazoline or their acid-addition salts may be administered orally with the dosage adjusted for the type of psoriasis and tolerances of the individual patient; the parenteral routes, especially the intravenous route, are most preferred. The usual mammalian dosage range for a 70 kg human subject is from 5 to 500 mg per day (0.07 mg to 7.1 mg per kg of weight per day), preferably 15 to 120 mg per day (0.2 mg to 1.7 mg per kg of weight per day), optionally in divided portions. Therapeutic agents of this type are generally prescribed for a specific time span, such as for a five day period depending upon the disease state being treated.
The above employed pharmaceutical compositions are produced by formulating the active compound in dosage unit form with a pharmaceutical carrier. Some examples of dosage unit forms are tablets, capsules, pills, powders, aqueous and non-aqueous oral solutions and suspensions, and parenteral solutions packaged in containers containing either one or some larger number of dosage units and capable of being subdivided into individual doses. Some examples of suitable pharmaceutical carriers, including pharmaceutical diluents, are gelatin capsules; sugars such as lactose and sucrose; starches such as corn starch and potato starch; cellulose derivatives such as sodium carboxymethyl cellulose, ethyl cellulose, methyl cellulose, and cellulose acetate phthalate; gelatin; talc; stearic acid; magnesium stearate; vegetable oils such as peanut oil, cottonseed oil, sesame oil, olive oil, corn oil, and oil of theobroma; propylene glycol; glycerine; sorbitol; polyethylene glycol; water; agar; alginic acid; isotonic saline, and phosphate buffer solutions; as well as other compatible substances normally used in pharmaceutical formulations. The compositions of the invention can also contain other components such as coloring agents, flavoring agents, and/or preservatives. These materials, if present, are usually used in relatively small amounts. The compositions can, if desired, also contain other therapeutic agents.
The percentage of the active ingredient in the foregoing compositions can be varied within wide limits but for practical purposes it is preferably present in a concentration of at least 10% in a solid composition and at least 2% in a primarily liquid composition. The most satisfactory compositions are those in which a much higher proportion of the active ingredient is present.
Claims (5)
1. A method for treating psoriasis in mammals which comprises administering an antipsoriatic-effective amount of 2,4-diamino-5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline, 2,4-diamino-5-chloro-6-[(3,4-dichloroanilino)methyl]quinazoline or a pharmaceutically acceptable salt thereof, to a mammal in need of said treatment.
2. The method of claim 1 wherein 0.07 mg to 7.1 mg/kg of weight per day of said compound is administered.
3. The method of claim 1 wherein said compound is 2,4-diamino-5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline monoacetate.
4. The method of claim 1 wherein said compound is 2,4-diamino-5-chloro-6-[(3,4-dichloroanilino)methyl]quinazoline monoacetate.
5. The method defined in claim 1 wherein said mammal is a human.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/206,596 US4391809A (en) | 1979-10-15 | 1980-11-13 | Methods for treating psoriasis |
| US07/112,919 US4853221A (en) | 1980-11-13 | 1987-10-23 | Method for treating non-small cell lung cancer, head and neck cancers and breast cancer |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8494479A | 1979-10-15 | 1979-10-15 | |
| US06/206,596 US4391809A (en) | 1979-10-15 | 1980-11-13 | Methods for treating psoriasis |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US8494479A Continuation | 1979-10-15 | 1979-10-15 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06471681 Division | 1982-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4391809A true US4391809A (en) | 1983-07-05 |
Family
ID=26771603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/206,596 Expired - Lifetime US4391809A (en) | 1979-10-15 | 1980-11-13 | Methods for treating psoriasis |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US4391809A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4694007A (en) * | 1986-05-20 | 1987-09-15 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Use of trimetrexate as antiparasitic agent |
| US4853221A (en) * | 1980-11-13 | 1989-08-01 | Warner-Lambert Company | Method for treating non-small cell lung cancer, head and neck cancers and breast cancer |
| US5430148A (en) * | 1992-03-31 | 1995-07-04 | Agouron Pharmaceuticals, Inc. | Antiproliferative quinazolines |
| US6017922A (en) * | 1998-05-18 | 2000-01-25 | U.S. Bioscience, Inc. | Thermally stable trimetrexates and processes for producing the same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1345502A (en) | 1972-07-06 | 1974-01-30 | Parke Davis & Co | Quinazoline compounds and processes for their production |
-
1980
- 1980-11-13 US US06/206,596 patent/US4391809A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1345502A (en) | 1972-07-06 | 1974-01-30 | Parke Davis & Co | Quinazoline compounds and processes for their production |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4853221A (en) * | 1980-11-13 | 1989-08-01 | Warner-Lambert Company | Method for treating non-small cell lung cancer, head and neck cancers and breast cancer |
| US4694007A (en) * | 1986-05-20 | 1987-09-15 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Use of trimetrexate as antiparasitic agent |
| US5430148A (en) * | 1992-03-31 | 1995-07-04 | Agouron Pharmaceuticals, Inc. | Antiproliferative quinazolines |
| US5707992A (en) * | 1992-03-31 | 1998-01-13 | Agouron Pharmaceuticals, Inc. | Antiproliferative quinazolines |
| US5885996A (en) * | 1992-03-31 | 1999-03-23 | Agouron Pharmaceuticals, Inc. | Antiproliferative quinazolines |
| SG93183A1 (en) * | 1992-03-31 | 2002-12-17 | Agouron Pharma | Antiproliferative quinazolines |
| US6017922A (en) * | 1998-05-18 | 2000-01-25 | U.S. Bioscience, Inc. | Thermally stable trimetrexates and processes for producing the same |
| US6258952B1 (en) | 1998-05-18 | 2001-07-10 | Medimmune Oncology, Inc. | Thermally stable trimetrexates and processes for producing the same |
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